C. Oliver Iselin's sailing career began with small,
over rigged boats known as sandbaggers. These were
wide, shoal boats on which capsize was always imminent.
He raced catboats in Long Island Sound and gained
a reputation as a keen racing skipper while still
in his teens.

Iselin, whose grandfather had amassed a large fortune
in the importing business, was elected to the New
York Yacht Club in 1877. Within ten years he found
himself a crew member aboard VOLUNTEER in 1887. This
experience no doubt led Iselin to successfully manage
the Cup yachts built by Herreshoff. He headed up the
VIGILANT syndicate in 1893, the same year the Earl
of Dunraven was elected to the New York Yacht Club
as an honorary member.

Aboard DEFENDER in the 1895 Cup challenge, Iselin
was at the center of the Earl of Dunraven controversy.
As his honor and that of his nation were in question,
Iselin put his fate in the hands of a New York Yacht
Club committee which vindicated him and gaulted Dunraven.
Being the great sportsman and yachtsman that Iselin
was, he offered to resail the entire match. Few could
equal his experience at racing and tuning these great
yachts and few could equal his sense of dignity and
honor in the face of poor sportsmanship.

In 1899, Iselin managed the syndicate that built
the Herreshoff yacht COLUMBIA at an astonishing cost
of $250,000. Coming out of retirement to manage the
RELIANCE in 1903, Iselin oversaw a perfect defense
that year. As manager of these Cup Defender syndicates,
he showed the embodiment of America's Cup spirit.
He understood the great yachts, commanded with authority,
and defended the America's Cup with honor and dignity.